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  • Bis(2-chloroethyl)amine hydrochloride CAS 821-48-7 BIS (2-CHLOROETHYL) AMINE HCL CAS no 821-48-7 2-chloro-n-(2-chloroethyl)-ethanaminhydrochloride

    Cas No: 821-48-7

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821-48-7 Usage

Chemical Properties

white to beige crystalline powder

Uses

Different sources of media describe the Uses of 821-48-7 differently. You can refer to the following data:
1. A cytotoxic metabolite of Cyclophosphamide; a deuterated analog of Nor-nitrogen mustard.
2. Bis(2-chloroethyl)amine hydrochloride is used as an intermediate in chemicals synthesis and building block for piperazine derivatives.

Safety Profile

A poison by inhalation,intraperitoneal, intramuscular, and subcutaneous routes.An experimental teratogen. Human mutation datareported. When heated to decomposition it emits toxicfumes of NH3, NOx, and Cl-.

Purification Methods

Crystallise the salt from Me2CO or MeOH/Et2O. The picrate has m 112-113o (from EtOH or Me2CO). [Mann J Chem Soc 464 1934, Ward J Am Chem Soc 57 915 1935,

Check Digit Verification of cas no

The CAS Registry Mumber 821-48-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 8,2 and 1 respectively; the second part has 2 digits, 4 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 821-48:
(5*8)+(4*2)+(3*1)+(2*4)+(1*8)=67
67 % 10 = 7
So 821-48-7 is a valid CAS Registry Number.
InChI:InChI=1/C4H9Cl2N/c5-1-3-7-4-2-6/h7H,1-4H2/p+1

821-48-7 Well-known Company Product Price

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  • Alfa Aesar

  • (A13118)  Bis(2-chloroethyl)amine hydrochloride, 98%   

  • 821-48-7

  • 50g

  • 204.0CNY

  • Detail
  • Alfa Aesar

  • (A13118)  Bis(2-chloroethyl)amine hydrochloride, 98%   

  • 821-48-7

  • 250g

  • 643.0CNY

  • Detail
  • Alfa Aesar

  • (A13118)  Bis(2-chloroethyl)amine hydrochloride, 98%   

  • 821-48-7

  • 1000g

  • 2369.0CNY

  • Detail

821-48-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name Bis(2-chloroethyl)amine hydrochloride

1.2 Other means of identification

Product number -
Other names BIS(2-CHLOROETHYL)AMINE HYDROCHLORIDE

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:821-48-7 SDS

821-48-7Synthetic route

2,2'-iminobis[ethanol]
111-42-2

2,2'-iminobis[ethanol]

bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

Conditions
ConditionsYield
With thionyl chloride In 1,2-dichloro-ethane at 50℃; for 3h;100%
With thionyl chloride In dichloromethane for 24h;100%
With thionyl chloride In chloroform at 50℃; for 4h; Temperature;98.8%
cyclophosphamide
50-18-0

cyclophosphamide

A

bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

B

Phosphoric acid mono-(3-amino-propyl) ester; hydrochloride

Phosphoric acid mono-(3-amino-propyl) ester; hydrochloride

Conditions
ConditionsYield
With hydrogenchloride at 37℃; pH 1.2;
N,N,N',N'-tetrakis(2-chloroethyl)methanediamine
15567-79-0

N,N,N',N'-tetrakis(2-chloroethyl)methanediamine

bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

Conditions
ConditionsYield
With acetyl chloride In dichloromethane Cooling;
bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

N,N-di(2-chloroethyl)amidophosphoric acid dichloride
127-88-8

N,N-di(2-chloroethyl)amidophosphoric acid dichloride

Conditions
ConditionsYield
With trichlorophosphate for 75h; Heating;100%
With trichlorophosphate100%
With trichlorophosphate Heating;93%
bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

bis(2-chloroethyl)carbamic acid ether
5467-15-2

bis(2-chloroethyl)carbamic acid ether

Conditions
ConditionsYield
With potassium carbonate In acetone for 4h; Heating / reflux;100%
With triethylamine In dichloromethane at 0℃; for 1.5h;99%
With triethylamine In dichloromethane at 0℃; for 1.5h;99%
With sodium hydroxide; water at 7 - 10℃;
bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

N,N-bis(2-chloroethyl)methanesulfonamide
54533-09-4

N,N-bis(2-chloroethyl)methanesulfonamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 15h;100%
With triethylamine In dichloromethane at 20℃; for 3h;94%
Stage #1: bis-(2-chloroethyl)amine hydrochloride With triethylamine In dichloromethane
Stage #2: methanesulfonyl chloride In dichloromethane at 20℃; for 3h;
94%
formaldehyd
50-00-0

formaldehyd

bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

mechlorethamine hydrochloride
55-86-7

mechlorethamine hydrochloride

Conditions
ConditionsYield
With formic acid at 100 - 120℃; for 3.33333h;100%
With formic acid In water at 100 - 120℃; for 3.33333h; Heating / reflux;100%
With formic acid In water at 100 - 120℃; for 3.33333h;100%
With formic acid In water 1a.) 100 deg C, 3 h, 1b.) 120 deg C, 20 min; Yield given;
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

N-(tert-butyloxycarbonyl)bis(2-chloroethyl)amine
118753-70-1

N-(tert-butyloxycarbonyl)bis(2-chloroethyl)amine

Conditions
ConditionsYield
With triethylamine100%
In dichloromethane100%
With sodium hydroxide In dichloromethane at 20℃; for 18.5h;100%
2-chloro-N-(3-hydroxypropyl)-3,5-dinitrobenzamide

2-chloro-N-(3-hydroxypropyl)-3,5-dinitrobenzamide

bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

2-[bis(2-chloroethyl)amino]-N-(3-hydroxypropyl)-3,5-dinitrobenzamide
851627-23-1

2-[bis(2-chloroethyl)amino]-N-(3-hydroxypropyl)-3,5-dinitrobenzamide

Conditions
ConditionsYield
With triethylamine In 1,4-dioxane at 50℃; for 24h;100%
2-chloro-N-(4-hydroxybutyl)-3,5-dinitrobenzamide
851627-28-6

2-chloro-N-(4-hydroxybutyl)-3,5-dinitrobenzamide

bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

2-[bis(2-chloroethyl)amino]-N-(4-hydroxybutyl)-3,5-dinitrobenzamide

2-[bis(2-chloroethyl)amino]-N-(4-hydroxybutyl)-3,5-dinitrobenzamide

Conditions
ConditionsYield
With triethylamine In 1,4-dioxane at 50℃; for 24h;100%
2-chloro-N-(4-hydroxybutyl)-3,5-dinitrobenzamide
851627-28-6

2-chloro-N-(4-hydroxybutyl)-3,5-dinitrobenzamide

bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

2-[bis(2-chloroethyl)amino]-N-(5-hydroxypentyl)-3,5-dinitrobenzamide
851627-29-7

2-[bis(2-chloroethyl)amino]-N-(5-hydroxypentyl)-3,5-dinitrobenzamide

Conditions
ConditionsYield
With triethylamine In 1,4-dioxane at 50℃; for 24h;100%
2-chloro-N-(6-hydroxyhexyl)-3,5-dinitrobenzamide
851627-20-8

2-chloro-N-(6-hydroxyhexyl)-3,5-dinitrobenzamide

bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

2-[bis(2-chloroethyl)amino]-N-(6-hydroxyhexyl)-3,5-dinitrobenzamide
851627-32-2

2-[bis(2-chloroethyl)amino]-N-(6-hydroxyhexyl)-3,5-dinitrobenzamide

Conditions
ConditionsYield
With triethylamine In 1,4-dioxane at 50℃; for 24h;100%
2-chloro-3,5-dinitrobenzoyl chloride
42747-54-6

2-chloro-3,5-dinitrobenzoyl chloride

bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

2-(bis(2-chloroethyl)amino)-N-(2-hydroxyethyl)-3,5-dinitrobenzamide

2-(bis(2-chloroethyl)amino)-N-(2-hydroxyethyl)-3,5-dinitrobenzamide

Conditions
ConditionsYield
With triethylamine In 1,4-dioxane at 50℃; for 24h; Product distribution / selectivity;100%
3,5-dibromo-4-chloroaniline

3,5-dibromo-4-chloroaniline

bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

1-(3,5-dibromo-4-chloro)phenylpiperazine
172732-40-0

1-(3,5-dibromo-4-chloro)phenylpiperazine

Conditions
ConditionsYield
In methanol; ethyl acetate; 1,2-dichloro-benzene100%
bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

2,2,2-Trichloroethyl chloroformate
17341-93-4

2,2,2-Trichloroethyl chloroformate

bis(2-chloroethyl)-2,2,2-trichloroethyl carbamate

bis(2-chloroethyl)-2,2,2-trichloroethyl carbamate

Conditions
ConditionsYield
Stage #1: bis-(2-chloroethyl)amine hydrochloride; 2,2,2-Trichloroethyl chloroformate In dichloromethane at 0℃; for 0.333333h;
Stage #2: With triethylamine In dichloromethane at 20℃; for 1.83333h;
100%
formaldehyd
50-00-0

formaldehyd

formic acid
64-18-6

formic acid

bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

mechlorethamine hydrochloride
55-86-7

mechlorethamine hydrochloride

Conditions
ConditionsYield
In water at 100℃; for 3h; Reflux;99%
3-(3-oxobenzo[d][1,2]selenazol-2(3H)-yl)propanoic acid

3-(3-oxobenzo[d][1,2]selenazol-2(3H)-yl)propanoic acid

bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

N,N-bis(2-chloroethyl)(benzisoselenazol-3-one-2-yl)propanamide

N,N-bis(2-chloroethyl)(benzisoselenazol-3-one-2-yl)propanamide

Conditions
ConditionsYield
Stage #1: 3-(3-oxobenzo[d][1,2]selenazol-2(3H)-yl)propanoic acid With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 5℃; for 0.25h;
Stage #2: bis-(2-chloroethyl)amine hydrochloride With benzotriazol-1-ol at 20℃;
99%
carbon dioxide
124-38-9

carbon dioxide

bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

3-(2-chloroethyl)-2-oxazolidinone
2508-01-2

3-(2-chloroethyl)-2-oxazolidinone

Conditions
ConditionsYield
With triethylamine In methanol at 20℃; for 1h;98.9%
With triethylamine In methanol at 20 - 30℃; for 0.5h;91.6%
With triethylamine In methanol at 20℃; for 1h; Inert atmosphere;82%
bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

Acetic acid 5-amino-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl ester
145124-55-6

Acetic acid 5-amino-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl ester

Acetic acid 5-piperazin-1-yl-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl ester
145124-53-4

Acetic acid 5-piperazin-1-yl-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl ester

Conditions
ConditionsYield
In chlorobenzene Heating;98%
4-amino-3-fluorophenol
399-95-1

4-amino-3-fluorophenol

bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

3-fluoro-4-(piperazin-1-yl)phenol hydrochloride

3-fluoro-4-(piperazin-1-yl)phenol hydrochloride

Conditions
ConditionsYield
In sulfolane at 150℃; for 16h;98%
2,3-difluoroanilline
4519-40-8

2,3-difluoroanilline

bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

1-(2,3-difluorophenyl)piperazine hydrochloride

1-(2,3-difluorophenyl)piperazine hydrochloride

Conditions
ConditionsYield
In diethylene glycol dimethyl ether at 130℃; for 15h;97.9%
3,5-dimethyl-1H-pyrazole
67-51-6

3,5-dimethyl-1H-pyrazole

bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

bis[2-(3,5-dimethyl-1H-pyrazol-1-yl)ethyl]amine
85650-01-7

bis[2-(3,5-dimethyl-1H-pyrazol-1-yl)ethyl]amine

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide97%
Stage #1: 3,5-dimethyl-1H-pyrazole With sodium In ethanol at 60℃; for 1h; Inert atmosphere;
Stage #2: bis-(2-chloroethyl)amine hydrochloride In ethanol at 60℃; for 12h;
64%
Stage #1: 3,5-dimethyl-1H-pyrazole With sodium In ethanol at 60℃; for 1h; Inert atmosphere;
Stage #2: bis-(2-chloroethyl)amine hydrochloride at 60℃; for 12h;
64%
bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

pyrographite
7440-44-0

pyrographite

N,N,N',N'-tetrakis(2-chloroethyl)phosphorodiamidic acid chloride
60106-92-5

N,N,N',N'-tetrakis(2-chloroethyl)phosphorodiamidic acid chloride

Conditions
ConditionsYield
With triethylamine; trichlorophosphate In toluene97%
With triethylamine; trichlorophosphate In toluene97%
bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

2-amino-8-fluorotryptanthrin

2-amino-8-fluorotryptanthrin

8-fluoro-2-(piperazin-1-yl)indolo[2,1-b]quinazoline-6,12-dione

8-fluoro-2-(piperazin-1-yl)indolo[2,1-b]quinazoline-6,12-dione

Conditions
ConditionsYield
With potassium carbonate In ethanol; water for 2h; Reagent/catalyst; Reflux;96.4%
3-benzyloxy-2-methyl-phenylamine
65361-82-2

3-benzyloxy-2-methyl-phenylamine

bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

1-(3-(benzyloxy)-2-methylphenyl)piperazine
871339-58-1

1-(3-(benzyloxy)-2-methylphenyl)piperazine

Conditions
ConditionsYield
With potassium carbonate In diethylene glycol dimethyl ether for 4h; Heating / reflux;96%
bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

2-Chloroaniline
95-51-2

2-Chloroaniline

1-(2-chlorophenyl)piperazine hydrochloride
41202-32-8

1-(2-chlorophenyl)piperazine hydrochloride

Conditions
ConditionsYield
With sodium carbonate In ethanol at 80℃; for 25h;96%
In sulfolane at 150℃; for 14h;90%
With 2-(2-methoxyethoxy)ethyl alcohol at 150℃; for 12h;85%
With 2-(2-methoxyethoxy)ethyl alcohol at 150℃; for 12h;85%
In diethylene glycol dimethyl ether at 130℃; for 15h;70%
bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

poly(3-azapentylenediselenide)

poly(3-azapentylenediselenide)

Conditions
ConditionsYield
With selenium; hydrazine hydrate; potassium hydroxide In water at 60 - 65℃; for 2h;96%
bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

benzyl chloroformate
501-53-1

benzyl chloroformate

bis(2-chloroethyl)carbamic acid benzyl ester
72791-76-5

bis(2-chloroethyl)carbamic acid benzyl ester

Conditions
ConditionsYield
Stage #1: benzyl chloroformate With sodium hydrogencarbonate In water at 0 - 20℃;
Stage #2: bis-(2-chloroethyl)amine hydrochloride In water at 0 - 20℃;
95%
Stage #1: bis-(2-chloroethyl)amine hydrochloride; benzyl chloroformate In dichloromethane at 0℃; for 0.166667h;
Stage #2: With triethylamine In dichloromethane at 20℃; for 2h;
95.5%
With triethylamine In dichloromethane at 0 - 20℃; for 6.5h;70%
bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

2-chloro-1,3,5-trimethyl-1,3,5-triaza-2ς3λ3-phosphorin-4,6-dione
77507-71-2

2-chloro-1,3,5-trimethyl-1,3,5-triaza-2ς3λ3-phosphorin-4,6-dione

1,3,5-Trimethyl-2-
149456-79-1

1,3,5-Trimethyl-2-

Conditions
ConditionsYield
With triethylamine In dichloromethane for 48h; Ambient temperature;95%
bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

m-Anisidine
536-90-3

m-Anisidine

4-(3-methoxyphenyl)piperazine
16015-71-7

4-(3-methoxyphenyl)piperazine

Conditions
ConditionsYield
In various solvent(s) at 150℃;95%
With potassium carbonate In butan-1-ol for 25h; Heating;67%
Reflux;
bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

(1-methyl-5-nitro-1H-imidazol-2-yl)methyl 4-nitrophenyl carbonate
263159-60-0

(1-methyl-5-nitro-1H-imidazol-2-yl)methyl 4-nitrophenyl carbonate

(1-methyl-5-nitro-1H-imidazol-2-yl)methyl bis(2-chloroethyl)carbamate

(1-methyl-5-nitro-1H-imidazol-2-yl)methyl bis(2-chloroethyl)carbamate

Conditions
ConditionsYield
With pyridine at 20℃; for 16h; Substitution;95%
5-fluoro-2-methoxy-aniline
1978-39-8

5-fluoro-2-methoxy-aniline

bis-(2-chloroethyl)amine hydrochloride
821-48-7

bis-(2-chloroethyl)amine hydrochloride

1-(4-fluoro-2-methoxyphenyl)piperazine
102392-11-0

1-(4-fluoro-2-methoxyphenyl)piperazine

Conditions
ConditionsYield
95%

821-48-7Relevant articles and documents

Synthesis and fluorescent properties of a novel dansyl-based fluorescent probe for Hg2+

Zuo-An, Xiao,Dan, Zhan,Xiao, Yang

, p. 108 - 110 (2014)

A novel turn-off fluorescent probe containing a dansyl fluorophore has been synthesised. Its recognition properties towards various metal ions have been studied by fluorescence spectrometry. The compound showed a high sensitivity and selectivity to Hg2+ ion and a complexation ratio towards Hg 2+ of 2 : 1. Its fluorescence intensity varied almost linearly versus the concentration of Hg2+ (0.8-8.4 μmol L-1), and the detection limit of Hg2+ was estimated to be 0.88 μmol L -1.

Synthesis, in vitro cytotoxicity and biological evaluation of twenty novel 1,3-benzenedisulfonyl piperazines as antiplatelet agents

Liu, Xiu-jie,Wang, Yan,Wang, Xiao,Zhang, Zhi-hao

, (2021/09/10)

In order to discover antiplatelet drug with novel structure and expand our research scope, total twenty 1,3-benzenedisulfonyl piperazines, were designed and synthesized. These target compounds were divided into two series, namely 4-methoxy-1,3-benzenedisulfonyl piperazines of series 1 and 4-ethoxy-1,3-benzenedisulfonyl piperazines of series 2. With adenosine diphosphate (ADP), arachidonic acid (AA) and collagen as inducers, respectively, the Born turbidimetric method was used to screen the antiplatelet activity in vitro of all target compounds at a concentration of 1.3 μM, with aspirin and picotamide as positive control drugs. And of which, the activities of five compounds for collagen were higher than both picotamide and aspirin. In ADP or AA channel, compounds with an inhibition rate greater than 33% were selected, and their corresponding IC50 values were obtained. According to the IC50, the in vitro activity of one compound for ADP was higher than picotamide, and for AA, two compounds were higher than two positive control drugs and other two compounds only higher than or equal to aspirin. The preliminary analysis of the structure-activity relationship of the target compounds involved in this study was completed. Further, eight compounds exhibiting higher activity in one or two test channels, were subjected to cytotoxicity test on mouse fibroblasts (L929) by CCK-8 method. The in vitro cytotoxicity of most test compounds showed less than or same to control drug picotamide at 10 μM, but at the higher concentration of 100 μM, merely two compounds exhibited higher cell survival rate than that of picotamide. In addition, compound N1,N3-di(4-ethoxy-1,3-phenylenedisulfonyl)bis(1-(m-tolyl)piperazine), which is delivery activity in the three test channels, and another compound N1,N3–di(4-methoxy-1,3-phenylenedisulfonyl)bis(1-(m-tolyl)piperazine), which has the lowest cytotoxic in vitro compound among series 1 and series 2, respectively, are found and selected for simulation analysis as two most likely to dock with the receptor P2Y12. Each of synthesized compounds in silico molecular property and ADME (absorption, distribution, metabolism and excretion) are predicted by using Molinspiration property engine v2018.10 and PreADMET online servers, respectively. Compared with other series of compounds in the previous stage, the two series compounds obtained after the introduction of piperazinyl have a similar in vitro activity.

Surface active SNS-based dicationic ionic liquids containing amphiphilic anions: Experimental and theoretical studies of their structures and organization in solution

Domingos, Josiel B.,Dupont, Jairton,Ferreira, Thuany M.,Monteiro, Wesley F.,Scholten, Jackson D.,Vieira, Michele O.,dos Santos, Francisco P.

, (2021/10/20)

Surface active ionic liquids (SAILs) have been reported as new media that collectively offer the advantages of the aqueous and oily phases. In particular, dicationic ionic liquids (DILs) have attracted much interests because their tunable physicochemical properties allow them to act as sustainable active catalysts in chemical reactions (CO2 conversion, esterification) and also as extraction media to remove drugs/pollutants from aqueous systems. In order to better understand this class of ILs, this work describes new strategies for the synthesis of SNS-based dicationic ILs containing amphiphilic anions ([C12SO4]-, [C12ESO4]-, [C12BSO3]- and [C12SAR]-) and the evaluation of their structural organization and aggregation level in solution. The results obtained by experimental techniques (FTIR, TGA, DSC, POM, ESI-MS, DLS and NMR) combined with those achieved by theoretical DFT calculations revealed that the anion has an important function to modulate the properties of the SNS-based ILs in solution, while the presence of a methyl group at the C2 position of the imidazolium ring seems to be not sufficient to change such physicochemical properties. The ILs containing the anion [C12BSO3]- showed a superior ionic organization in solution due to the cationic aggregates observed in the ESI(+) mode and the large size of aggregates observed by DLS. This behavior may be assigned to a close proximity of the cationic imidazolium ring and the aromatic ring in the anion (π-π interaction), and by NMR analysis (ROESY and DOSY) it was possible to confirm interactions between cation and anion. Therefore, the theoretical and experimental results obtained for the SNS-based dicationic ILs containing amphiphilic anions indicate that these ILs can be applied as media in both pure and/or solution systems for many sustainable applications.

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